NPASS Compound

Natural Product: NPC473279

Natural Product ID	NPC473279
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Berenjenol
IUPAC Name	n.a.
Synonyms	berenjenol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL390981
PubChem CID	16681372
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 85 90 0 0 0 0 0 0 0 0999 V2000 7.5958 1.7498 -0.5127 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9896 0.6380 0.2662 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4939 0.8575 0.5353 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4065 2.1531 1.3240 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8537 1.0465 -0.8099 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3329 0.8437 -0.7074 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1728 -0.5230 -0.0554 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6715 -0.3946 1.3111 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0741 -0.1978 1.2555 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8644 -1.0980 -0.3828 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6534 -2.4585 0.2522 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1438 -2.5640 0.5561 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3913 -1.5475 -0.4272 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6070 -0.4414 -0.0502 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5950 -0.2124 1.4440 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1293 0.7550 -0.7253 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1050 1.2353 0.0428 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1406 0.1722 0.2258 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7954 -1.1621 -0.3858 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4989 -1.0851 -1.7223 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9855 -1.3368 -1.4275 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4667 -0.0585 -0.8093 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5051 0.6422 0.0403 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1052 0.2309 1.3823 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7905 2.1497 -0.0802 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3012 2.2911 -0.1562 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0290 1.1920 0.5624 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7846 -0.1757 -0.0902 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8689 -0.3777 -1.1183 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8271 -1.1930 0.9789 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6428 1.1912 1.8974 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1245 -2.1999 -1.7565 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1863 -0.7198 -0.4166 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0706 1.2930 -1.4301 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4712 2.1939 0.0427 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9292 2.5697 -0.7747 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5021 0.5524 1.2466 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3665 2.3848 1.8476 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2147 3.0221 0.6606 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6315 2.0938 2.1310 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9805 2.0949 -1.1465 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2307 0.3877 -1.5908 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0195 1.6340 0.0273 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8894 0.9235 -1.6896 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9312 -1.1737 -0.6033 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6268 -1.3337 1.9418 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2981 0.4881 1.8896 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8905 -1.1607 -1.5166 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0426 -3.3018 -0.3100 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1460 -2.5260 1.2476 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1945 -3.5808 0.3180 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0728 -2.3219 1.5990 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3036 -0.8417 2.0013 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3579 -0.3279 1.9380 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9399 0.8463 1.6348 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7801 1.6260 -0.7983 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1648 0.4992 -1.7708 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4856 2.1036 -0.5644 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8218 1.6448 1.0081 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3454 -1.9316 0.2368 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4695 -0.0439 -2.1575 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2222 -1.7550 -2.4965 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4640 -1.5184 -2.4115 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0261 -2.2120 -0.7910 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6942 0.6086 -1.6994 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3248 -0.7526 1.8288 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8844 1.0015 2.1763 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4134 2.5253 -1.0767 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3518 2.7116 0.7562 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5982 3.2416 0.3133 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6706 2.3273 -1.2010 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1007 1.4115 0.5128 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1027 -1.4587 -1.2438 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5153 -0.0192 -2.1104 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7725 0.2065 -0.8337 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7204 -0.7330 2.0050 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8665 -1.6343 0.9982 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1379 -2.0258 0.9063 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3897 1.3767 2.5099 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8063 -2.8077 -1.8155 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8827 -3.0523 -1.7705 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2037 -1.5411 -2.6152 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3958 -1.4322 -0.1062 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1559 -1.1622 -0.1049 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2237 -0.5226 -1.4905 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 6 3 4 1 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 7 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 1 14 16 1 0 16 17 1 0 18 17 1 1 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 1 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 27 31 1 0 13 32 1 6 2 33 1 0 9 3 1 0 14 10 1 0 24 18 1 0 19 13 1 0 28 22 1 0 23 18 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 0 4 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 7 45 1 0 8 46 1 0 8 47 1 0 10 48 1 6 11 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 15 53 1 0 15 54 1 0 15 55 1 0 16 56 1 0 16 57 1 0 17 58 1 0 17 59 1 0 19 60 1 1 20 61 1 0 20 62 1 0 21 63 1 0 21 64 1 0 22 65 1 6 24 66 1 0 24 67 1 0 25 68 1 0 25 69 1 0 26 70 1 0 26 71 1 0 27 72 1 1 29 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 31 79 1 0 32 80 1 0 32 81 1 0 32 82 1 0 33 83 1 0 33 84 1 0 33 85 1 0 M END

Standard InCHIKey	QGUCSIMOQIAADS-HEHMHTDASA-N
Standard InCHI	InChI=1S/C31H52O2/c1-20(2)29(7)14-10-21(18-33-29)22-11-13-28(6)24-9-8-23-26(3,4)25(32)12-15-30(23)19-31(24,30)17-16-27(22,28)5/h20-25,32H,8-19H2,1-7H3/t21?,22-,23+,24+,25+,27-,28+,29-,30-,31+/m1/s1
SMILES	CC([C@@]1(C)CCC(CO1)[C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@@H](C2(C)C)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	456.4	Volume:	510.974 ? Van der Waals volume.
Dense:	0.893	LogP:	4.418 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.796 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.666 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	28.0
TPSA:	29.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.463	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.705	Fsp³:	1.0
MCE-18:	157.161 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.823	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.416	Promiscuous compounds:	0.015

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.103	MDCK Permeability:	-4.83
Pgp-inhibitor:	0.091	Pgp-substrate:	0.044
PAMPA:	0.428 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.017	30% Bioavailability (F30%):	0.018
50% Bioavailability (F50%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.98	MRP1:	0.025
Plasma Protein Binding (PPB):	88.623%	Volume Distribution (VD):	0.049
Fu:	13.101% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.973	BCRP inhibitor:	0.998
BSEP inhibitor:	0.768

ADMET: Metabolism

CYP1A2-inhibitor:	0.045	CYP1A2-substrate:	0.045
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.525
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.876
CYP2D6-inhibitor:	0.922	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.174
HLM stability:	0.956 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

18.904

Half-life (T1/2):

1.134

ADMET: Toxicity

hERG Blockers:	0.258	hERG Blockers (10um):	0.499
Human Hepatotoxicity (H-HT):	0.505	Drug-induced Liver Injury (DILI):	0.023
AMES Toxicity:	0.24	Rat Oral Acute Toxicity:	0.449
Maximum Recommended Daily Dose:	0.867	Skin Sensitization:	0.906
Carcinogencity:	0.813	Eye Corrosion:	0.0
Eye Irritation:	0.062	Respiratory Toxicity:	0.365
Drug-induced Neurotoxicity:	0.02	Ototoxicity:	0.621
Hematotoxicity:	0.05	Drug-induced Nephrotoxicity:	0.074
Genotoxicity:	0.065	RPMI-8226 Immunitoxicity:	0.094
A549 Cytotoxicity:	0.195	Hek293 Cytotoxicity:	0.656
BCF:	2.887 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.992 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.796 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.84 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33511	oxandra cf. xylopioides	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17402783]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Activity	3

Activity Type	# Activity
Organism	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	44.0	%	DrugMatrix in vivo data: Pathology
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	64.0	%	DrugMatrix in vivo data: Pathology
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	51.0	%	PMID[17461599]

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC473279 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	25206
0.1-0.2	22157
0.2-0.3	2124
0.3-0.4	287
0.4-0.5	44
0.5-0.6	34
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.6545	Remote Similarity	NPC472341
0.6538	Remote Similarity	NPC607543
0.6296	Remote Similarity	NPC254509
0.6182	Remote Similarity	NPC472342
0.6182	Remote Similarity	NPC195530
0.6038	Remote Similarity	NPC41577
0.5926	Remote Similarity	NPC299948
0.5926	Remote Similarity	NPC241085
0.5893	Remote Similarity	NPC273366
0.5818	Remote Similarity	NPC331618
0.5818	Remote Similarity	NPC257191
0.5818	Remote Similarity	NPC196358
0.5789	Remote Similarity	NPC70982
0.5789	Remote Similarity	NPC22133
0.5763	Remote Similarity	NPC473238
0.5763	Remote Similarity	NPC134481
0.5738	Remote Similarity	NPC307776
0.5738	Remote Similarity	NPC483817
0.5714	Remote Similarity	NPC200243
0.5714	Remote Similarity	NPC85346
0.5714	Remote Similarity	NPC65897
0.5714	Remote Similarity	NPC82623
0.5714	Remote Similarity	NPC80237
0.5714	Remote Similarity	NPC604180
0.569	Remote Similarity	NPC76518
0.569	Remote Similarity	NPC67872
0.5614	Remote Similarity	NPC470830
0.5614	Remote Similarity	NPC479659
0.5593	Remote Similarity	NPC12722
0.55	Remote Similarity	NPC89747
0.5323	Remote Similarity	NPC18384
0.5323	Remote Similarity	NPC110923
0.5323	Remote Similarity	NPC476186
0.5323	Remote Similarity	NPC74296
0.5231	Remote Similarity	NPC472745
0.5156	Remote Similarity	NPC195366
0.5156	Remote Similarity	NPC85379
0.5156	Remote Similarity	NPC144909
0.5156	Remote Similarity	NPC476304
0.5156	Remote Similarity	NPC114743

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC473279 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7318
0.1-0.2	1795
0.2-0.3	36
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data